Three adults, two women and one man, are smiling and enjoying glasses of red wine at an outdoor table in a park setting. A bottle of red wine and two glasses are on the table in front of them.
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Chesapeake Virginia Wine Festival

15th annual wine festival supporting local charities.

About

Uncork a good time at the 15th annual Chesapeake Virginia Wine Festival. Sample unlimited pours from over 20 Virginia wineries and explore international selections. Enjoy live music and chef-driven bites in a festive outdoor setting. This event supports local charities, making every sip count.

Our Take

Scare Factor

👻 (1/5)

Family Friendly

👶 👶 (2/5)

Best For

Wine enthusiasts and adults seeking a festive outdoor experience.

Vibe

Relaxed, celebratory, community-focused

Energy Level

Moderate

Budget

$$

Photo Friendly

High

Weather Sensitivity

Low (rain or shine)

Special Events & Promotions

  • 100% of ticket price goes to local impact through Rotary Club of Chesapeake Community Charities
  • Reserved Tables and Private Chalets available (sold out in 2024)
  • Unlimited tastings from 20+ Virginia wineries and International Wine Village

Tags

wine tastingfood truckscraft beer festivalcommunity eventcharity eventlive musicfall festival

Always check the official website for the most current information.

We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly.

Location

900 City Park Dr
Chesapeake, VA
23320

Event Details

Pricing

$45.00 + $1.50 Service Fee (Advance Tasting Ticket)

Duration

6 hours

Ages

21 and Over

Timed Entry

No

Featured Performers

  • Lewis and Kaycie McHehee
  • Borderline Crazy
  • The River Boyz

Organizer

Rotary Club of Chesapeake

Practical Information

Parking

Free on-site parking is available.

Accessibility

Accessible parking is available on a first-come, first-served basis for vehicles displaying disability permits.

Pet Policy

Service animals only

Food & Drink

Specialty food vendors, craft beer garden, wine apparel, and wine accessories.

Quick Actions

Tips & Advice

  • Bring a blanket or lawn chair for comfortable seating in designated areas, but leave beach umbrellas and pop-up tents at home.
  • Coolers and picnic baskets are permitted but will be searched at the entrance; plan to enjoy the diverse food vendor offerings.
  • Consider booking a reserved table or private chalet early, as they sold out in previous years.
  • Since this is a rain-or-shine event, check the weather forecast and dress accordingly, but personal umbrellas are allowed.
  • Arrive early to take advantage of free on-site parking, as it is available on a first-come, first-served basis.

Frequently Asked Questions

How do I contact the Festival?

You can email the festival organizers at chesapeakevawinefestival@gmail.com.

Is this an all-ages event?

No, attendees must be at least 21 years of age with a valid photo ID to purchase and/or consume alcoholic beverages.

What if it rains?

This is a rain-or-shine event. Personal umbrellas are permitted, but beach umbrellas and pop-up tents are not.

Can I bring my pet?

Only service animals trained to assist disabled persons are allowed into the event. No other pets are permitted.

What items are not permitted?

Prohibited items include beach umbrellas, pop-up tents, personal tables, grills, weapons, illegal substances, outside alcohol, skateboards, scooters, bicycles, fireworks, explosives, and unauthorized vendors.

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Contributors & Updates

Last Updated: Nov 11, 2025
Original Submitter: Sep 17, 2025 The Halloween Events Near Me editorial team

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